WO2014030846A1 - 하드코팅 필름 - Google Patents

하드코팅 필름 Download PDF

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Publication number
WO2014030846A1
WO2014030846A1 PCT/KR2013/006775 KR2013006775W WO2014030846A1 WO 2014030846 A1 WO2014030846 A1 WO 2014030846A1 KR 2013006775 W KR2013006775 W KR 2013006775W WO 2014030846 A1 WO2014030846 A1 WO 2014030846A1
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WO
WIPO (PCT)
Prior art keywords
hard coating
film
coating film
hard coat
photocurable
Prior art date
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PCT/KR2013/006775
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English (en)
French (fr)
Korean (ko)
Inventor
강준구
장영래
홍성돈
정순화
허은규
Original Assignee
주식회사 엘지화학
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Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201380054065.8A priority Critical patent/CN104736615B/zh
Priority to JP2015528384A priority patent/JP6276764B2/ja
Priority to EP13830681.6A priority patent/EP2873694A4/en
Priority to US14/422,437 priority patent/US9909026B2/en
Publication of WO2014030846A1 publication Critical patent/WO2014030846A1/ko

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/16—Cyclodextrin; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D135/02—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2433/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/10—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet
    • C09J2301/16—Additional features of adhesives in the form of films or foils characterized by the structural features of the adhesive tape or sheet by the structure of the carrier layer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24917—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including metal layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/269—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension including synthetic resin or polymer layer or component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848—Three or more layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/10—Scrim [e.g., open net or mesh, gauze, loose or open weave or knit, etc.]

Definitions

  • the present invention relates to a hard coat film. More specifically, the present invention relates to a hard coat film exhibiting high hardness and excellent properties.
  • Glass or tempered glass is generally used as a material having excellent mechanical properties in the display window or the front plate of the mobile device.
  • the glass causes the mobile device to be heavier due to its own weight, and there is a problem of breakage due to the external stratification.
  • Plastic resin is being researched as a substitute material for glass.
  • Plastic resin compositions are suitable for the trend toward a lighter mobile device because they are lightweight and less prone to breakage.
  • compositions have been proposed for coating a hard coat layer on a support substrate to achieve compositions having high hardness and wear resistance properties.
  • a method of increasing the thickness of the hard coating layer may be considered.
  • the surface hardness may be increased.
  • wrinkles or curls increase due to hardening shrinkage of the hard coating layer, cracks or peeling of the hard coating layer are likely to occur. Is not easy.
  • Korean Unexamined Patent Publication No. 2010-0041992 discloses a hard coating composition using a binder resin including a monomer and excluding an ultraviolet curable polyurethane acrylate oligomer.
  • the hard coating composition disclosed above is not strong enough to replace the glass panel of the display with a pencil hardness of about 3H.
  • the present invention provides a hard coating film having high hardness and excellent properties.
  • the hard coating film of the present invention exhibits high hardness, layer resistance, scratch resistance, and high transparency to replace glass in cover panels or device substrates of mobile communication terminals, touch panels of smartphones or tablet PCs, and various displays. Can be used for purposes.
  • the second photocurable crosslink And a second hard coat layer comprising inorganic fine particles dispersed in the second photocurable crosslinked copolymer.
  • the support substrate A first hard coat layer formed on one surface of the support substrate and including a first photocurable crosslinked copolymer; And a second hard coat layer formed on the other side of the support substrate and including a second photocurable crosslinked copolymer and inorganic fine particles dispersed in the first photocurable crosslinkable copolymer. to provide.
  • the support substrate on which the first and second hard coat layers are formed is a transparent plastic resin that is commonly used, and is not particularly limited to a method or material for preparing a support substrate such as a stretched film or an unstretched film. Can be used.
  • the support substrate may include, for example, polyester such as polyethylene terephthalate (PET), polyethylene such as ethylene vinyl acetate (EVA) polyethylene), cyclic olefin polymers (cyclic olefin polymers, COP), cyclic olefin copolymers (cyclic olefin copolymers, COC), Polyacrylate (PAC), polycarbonate (PC), polyethylene (PE), polymethylmethacrylate (PMMA), polyetheretherketon (PEEK), poly Ethylenenaphthalate (PEN), polyetherimide (PEI), polyimide (PI), triacetylcellulose (TAC), methyl methacrylate (MMA), or fluorine resin
  • the film may include.
  • the support substrate may be a single layer or a multilayer structure including two or more substrates made of the same or different materials as necessary, but is not particularly limited.
  • the support substrate is a multi-layered structure of polyethylene terephthalate (PET), two or more layers formed by coextrusion of polymethyl methacrylate (PMMA) / polycarbonate (PC) It can be popular.
  • PET polyethylene terephthalate
  • PMMA polymethyl methacrylate
  • PC polycarbonate
  • the support substrate may be a substrate including a copolymer of poly methyl methacrylate (PMMA) and polycarbonate (PC).
  • PMMA poly methyl methacrylate
  • PC polycarbonate
  • the thickness of the support substrate is not particularly limited, but a support substrate having a thickness of about 30 to about 1,200 / ffli, or about 50 to about 800 may be used.
  • the hard coat film of the present invention includes first and second hard coat layers formed on both sides of the support substrate, respectively.
  • the first hard coat layer includes a first photocurable crosslinked copolymer.
  • the first photocurable crosslinked copolymer may be a crosslinked copolymer of 1 to 6 functional acrylate monomers and a photocurable elastomer.
  • the acrylate-based means not only acrylate but also methacrylate, or a derivative in which a substituent is introduced into acrylate or methacrylate.
  • the said photocurable elastomer is an ultraviolet-ray It means a polymer material that exhibits elasticity and includes a functional group capable of crosslinking polymerization by irradiation.
  • the photocurable elastomer is at least about 15%, for example from about 15 to about 200%, or from about 20 to about 200%, or from about 20 to about as measured by ASTM D638. It can have an elongation of 150%.
  • the photocurable elastomer may be cross-polymerized with the 1 to 6 functional acrylate monomers to form a first hard coat layer after curing, and may provide flexibility and layer resistance to the first hard coat layer formed. .
  • the photocurable elastomer may be a polymer or oligomer having a weight average molecular weight in the range of about 1,000 to about 600,000 g / mol, or about 10,000 to about 600,000 g / mol.
  • the photocurable elastomer may be, for example, one or more selected from the group consisting of polycaprolactone, urethane acrylate polymers, and plerotacein.
  • polycaprolactone is formed by ring-opening polymerization of caprolactone and has excellent physical properties such as flexibility, impact resistance, and durability.
  • the urethane acrylate polymer has excellent elasticity and durability, including urethane bonds.
  • the polyrotaxane refers to a compound in which a dumbbell shaped molecule and a cyclic compound are structurally fitted.
  • the dumbbell-shaped molecule includes a constant linear molecule and a blocking group disposed at both ends of the linear molecule, the linear molecule penetrates inside the cyclic compound, and the cyclic compound can move along the linear molecule. And the departure is prevented by the blocker.
  • the cyclic compound may be used without any limitation as long as it has a size enough to penetrate or surround the linear molecule, and may be a hydroxyl group, an amino group, a carboxyl group, a thiol group, or an aldehyde group that may react with other polymers or compounds. It may also contain a functional group. Specific examples of such cyclic compounds include ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, or a combination thereof. ⁇ .
  • a compound having a straight chain form having a molecular weight of a predetermined or more may be used without great limitation, but a polyalkylene compound or a polylactone compound may be used.
  • a polyoxyalkylene compound containing a oxyalkylene repeating unit having 1 to 8 carbon atoms or a polylactone compound having a lactone repeating unit having 3 to 10 carbon atoms may be used.
  • the blockade group may be appropriately adjusted according to the properties of the rotacein compound to be produced, for example, one selected from the group consisting of dinitrophenyl group, cyclodextrin group, ammantane group, triyl group, fluorescein group and pyrene group or Two or more kinds can be used.
  • the first hard coat layer includes the photocurable elastomer to photocurable to impart high hardness and flexibility to the first hard coat layer, in particular to prevent damage by the outer layer It is possible to secure excellent layer resistance.
  • the 1 to 6 functional acrylate monomers are, for example, hydroxyethyl acrylate ( ⁇ ), hydroxyethyl methacrylate ( ⁇ ), nucleic acid dididiacrylate (HDD A), tripropylene glycol diacrylate (TPGD A), ethylene glycol diacrylate (EGDA), trimethylolpropane triacrylate (TMPTA), trimethylolpropane specific triacrylate (TMPEOTA), glycerin propoxylated triacrylate (GPTA), pentaerythreat Tetraacrylate (PET A), or dipentaerythroxy to nuxaacrylate (DPHA), etc. are mentioned.
  • the 1 to 6 functional acrylate monomers may be used alone or in combination with each other.
  • the first photocurable crosslinked copolymer may be a crosslinked copolymer in which the photocurable elastomer and a 1 to 6 functional acrylate monomer are crosslinked.
  • the first photocurable crosslinked copolymer is 20 to 80 parts by weight of the photocurable elastomer when the total weight of the first photocurable crosslinked copolymer is 100 parts by weight, wherein 1 80 to 20 parts by weight of the 6 to 6 functional acrylate monomer, or 20 to 60 parts by weight of the photocurable elastomer, 40 to 80 parts by weight of the 1 to 6 functional acrylate monomer is a copolymer crosslinked Can be.
  • the first hard coat layer may include a first photocurable crosslinked copolymer crosslinked with a high content of a high elastic photocurable elastomer, thereby achieving high layer resistance and good physical properties.
  • the first hard coating filler is at least 50 / m, for example about 50 to about 300 // m, or about 50 to about 200 / zm, or about 50 to about 150 ⁇ , Or about 70 to about 150 microns.
  • the first hard coating layer in addition to the above-mentioned first photocurable cross-linked copolymer, further include additives commonly used in the art to which the present invention belongs, such as surfactants, anti-yellowing agents, leveling agents, antifouling agents Can be.
  • additives commonly used in the art to which the present invention belongs such as surfactants, anti-yellowing agents, leveling agents, antifouling agents Can be.
  • the content can be variously adjusted within the range of not lowering the physical properties of the hard coat film of the present invention, it is not particularly limited, for example, about 0.1 to 100 parts by weight of the first photocurable crosslinked copolymer, About 10 parts by weight.
  • the first hard coating layer may include a surfactant as an additive, and the surfactant may include 1 to 2 functional fluorine-based acrylates, fluorine-based surfactants or silicone-based. Surfactant can be the best.
  • the surfactant may be included in the form of being dispersed or crosslinked in the crosslinked copolymer.
  • a yellowing inhibitor may be included as the additive, and the yellowing inhibitor may include a benzophenone compound or a benzotriazole compound.
  • the first hard coat layer may comprise the 1 to 6 functional acrylate monomers, the photocurable elastomer, the photoinitiator, the organic solvent, and optionally It may be formed by applying a first hard coating composition comprising an additive on a support substrate and then photocuring.
  • photoinitiator examples include 1-hydroxycyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone and 2-hydroxy-1- [4- (2-hydroxy Oxy) phenyl] -2-methyl-1-propanone, methylbenzoylformate, ⁇ , ⁇ -dimethoxy- ⁇ -phenylacetophenone, 2-benzoyl-2- (dimethylamino) -1- [4- ( 4-morpholinyl) phenyl] -1-butanone, 2-methyl-1- [4- (methylthio) phenyl] -2- (4-morpholinyl) -1-propanone diphenyl (2, 4,6-tri methylbenzoyl) -phosphine oxide, or bis (2,4,6-tri methylbenzoyl) -phenylphosphine oxide, and the like, but are not limited thereto.
  • Irgacure 184 Commercially available products include Irgacure 184, Irgacure 500, Irgacure 651, Irgacure 369, Irgacure 907, Darocur 1173, Darocur MBF, Irgacure 819, Darocur TPO, Irgacure 907, and Esacure KIP 100F.
  • These photoinitiators can be used individually or in mixture of 2 or more types different from each other.
  • organic solvent examples include alcohol solvents such as methanol, ethanol, isopropyl alcohol and butanol, 2-methoxytane, alkoxy alcohol solvents such as 2-ethoxy ethanol and 1-methoxy-2-propanol, acetone Ketone-based solvents such as methyl ethyl ketone, methyl isobutyl ketone methyl propyl ketone, cyclonucleanone propylene glycol monopropyl ether, propylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol monopropyl ether Ethylene Glycol Monobutyl Ether, Diethylene Glycol Monomethyl Ether Diethyl Glycol Monoethyl Ether, Diethyl Glycol Monopropyl Ether, Diethyl Glycol Monobutyl Ether, Diethylene Glycol-2-E Ether solvents such as ether, and aromatic solvents such as benzene, toluene and
  • the organic solvent with respect to a solid content including the 1 to 6 functional acrylate monomer, photocurable elastomer, photoinitiator, and other additives the solid content: weight ratio of the organic solvent About 70: 30 to about 99: 1.
  • a high viscosity composition can be obtained, and accordingly, a thick coating can be performed to obtain a first film having a high thickness, for example, 50 / im or more.
  • a hard coat layer can be formed.
  • the second hard coat layer is formed on the other side of the support substrate, the inorganic photo-curable crosslinked copolymer, and the inorganic fine particles dispersed in the second photocurable crosslinked copolymer Contains ruler
  • the second photocurable crosslinked copolymer may be a crosslinked copolymer of a 3 to 6 functional acrylate monomer.
  • the 3 to 6 functional acrylate monomers include trimethylolpropane triacrylate (TMPTA), trimethyl propane ethoxy triacrylate (TMPEOTA), glycerin propoxylated triacrylate (GPTA) : pentaerytri The tetraacrylate (PETA) or the dipenta to nutriacrylate (DPHA) etc. are mentioned.
  • TMPTA trimethylolpropane triacrylate
  • TMPEOTA trimethyl propane ethoxy triacrylate
  • GPTA glycerin propoxylated triacrylate
  • PETA tetraacrylate
  • DPHA dipenta to nutriacrylate
  • the 3 to 6 functional acrylate monomers may be used alone or in combination with each other.
  • the second photocurable crosslinked copolymer may be a crosslinked copolymer in which the 3 to 6 functional acrylate monomers are cross-polymerized with each other.
  • the second photocurable crosslinked copolymer may be a crosslinked copolymer in which 1 to 2 functional acrylate monomers are cross-polymerized in addition to the 3 to 6 functional acrylate monomers. have.
  • the 1 to 2 functional acrylate monomers are, for example, hydroxyethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA), nucleic acid didi diacrylate (HDD A), or tripropylene glycol diacrylate. (TPGDA), ethylene glycol diacrylate (EGDA), etc. are mentioned.
  • the 1 to 2 functional acrylate monomers may also be used alone or in combination with each other.
  • the second photocurable crosslinked copolymer is a crosslinked copolymer in which 1 to 2 functional acrylate monomers and 3 to 6 functional acrylate monomers are crosslinked, the 1 to 2 functional acrylate monomers and the 3
  • the content ratio of the 6 to 6 functional acrylate monomer is not particularly limited, but according to an embodiment of the present invention, the 1 to 2 functional
  • the acrylate monomer and the 3 to 6 functional acrylate monomer are in a weight ratio of about 1:99 to about 50:50, or about 10:90 to about 50:50, or about 20:80 to about 40:60. May be included.
  • the 1 to 2 functional acrylate monomer and 3 to 6 functional acrylate monomer in the weight ratio, it is possible to give high hardness and flexibility without deterioration of other physical properties such as curling properties and light resistance.
  • the second hard coat layer includes inorganic particles dispersed in the second photocurable crosslinked copolymer.
  • the inorganic fine particles having a particle size of nanoscale for example, the particle size of about 100 nm or less, or about 10 to about 100 nm, or about 10 to about 50 nm Nanoparticles can be used.
  • the inorganic fine particles for example, silica fine particles, aluminum oxide particles, titanium oxide particles, or zinc oxide particles may be used. By including the inorganic fine particles, it is possible to further improve the hardness of the hard coat film.
  • the second hard coat layer is about 40 to about 90 parts by weight of the second photocurable crosslinked copolymer and about 10 to about 60 parts by weight based on 100 parts by weight of the second hard coat layer. It may comprise inorganic particulates, or may comprise about 50 to about 80 parts by weight of the second photocurable crosslinked copolymer and about 20 to about 50 parts by weight of inorganic particulates. By including the second photocurable crosslinked copolymer and the inorganic fine particles in the above range can be formed a hard coating film of excellent physical properties.
  • the second hard coating layer is 50 / m or more, for example about 50 to about 300 / ⁇ , or about 50 to about 200 / ⁇ , or about 50 to about 150, or about 70 to about 150 / zm.
  • the second hard coating layer is commonly used in the technical field to which the present invention belongs, such as the above-mentioned second photocurable crosslinked copolymer and inorganic fine particles, surfactant, anti-yellowing agent, leveling agent, antifouling agent, etc. It may further include an additive.
  • the content is the physical properties of the hard coat film of the present invention Since it can be variously adjusted in the range which does not reduce, it does not restrict
  • the second hard coating layer may include a surfactant as an additive, and the surfactant may be a 1 to 2 functional fluorine acrylate, a fluorine surfactant or a silicone surfactant. Can be.
  • the surfactant may be included in the form of being dispersed or crosslinked in the crosslinked copolymer.
  • the additive may include a yellowing inhibitor, and the yellowing inhibitor may include a benzophenone compound or a benzotriazole compound.
  • the second hard coat layer is formed by photocuring a second hard coating composition comprising a binder monomer, an inorganic fine particle, a photoinitiator, an organic solvent, and optionally an additive including the 3 to 6 functional acrylate monomers. can do.
  • the photoinitiator the same or different material as the photoinitiator used in the first hard coating composition may be used, and examples of specific materials are as described in the first hard coating composition.
  • these photoinitiators can be used individually or in mixture of 2 or more types different from each other.
  • the organic solvent the same or different materials as the organic solvent used in the first hard coating composition may be used, and examples of specific materials are as described in the first hard coating composition.
  • the second from a hard coating composition, the organic solvent of the binder monomer, wherein the inorganic fine particles, for ⁇ a solid content containing the photoinitiator and other additives, the solids content for: the weight ratio of the organic solvent is about 70: to 30 about 99: 1.
  • a high viscosity composition can be obtained, thereby enabling thick coating, thereby allowing the second hard coating layer to have a high thickness, for example, 50zm or more. Can be formed.
  • the hard coat film of the present invention is on at least one hard coat layer of the first hard coat layer or the second hard coat layer. At least one further comprising a plastic resin film, an adhesive film, a release film, a conductive film, a conductive layer, a coating layer, a cured resin layer, a non-conductive film, a metal mesh layer or a patterned metal layer, a film, or a film. can do.
  • the layer, film, film or the like may be in any form of a single layer, a double layer or a laminate.
  • the layer, film, or film may be laminated on the hard coating layer by laminating a freestanding film using an adhesive or an adhesive film, or by coating, depositing, sputtering, or the like. The invention is not limited thereto.
  • the other layer, film, or film may be formed in direct contact with the first hard coat layer in order to protect the other layer, film, or film from the outer lamination and ensure scratch resistance by friction.
  • the hard coat film according to the present invention may be formed by applying the above-described first and second hard coat compositions to the one side and the back side of the supporting substrate, respectively or sequentially applying the both sides of the supporting substrate to photocuring. have.
  • the hard coat film may be prepared by the following method.
  • a first hard coat composition including the above-described components is applied on one surface of the support substrate and then photocured to form a first hard coat layer.
  • the first hard coat layer may be formed by a conventional method used in the art.
  • a first hard coating composition comprising the aforementioned components is applied to one side of the support substrate.
  • the method of applying the first hard coating composition is not particularly limited as long as it can be used in the technical field to which the present technology belongs, for example bar coating method, knife coating method, coating method, blade coating method, die coating Method, microgravure coating method, comma coating method, slot die coating method, lip coating method, or solution casting casting) method and the like.
  • the first hard coat layer is formed by irradiating the applied first hard coat composition with ultraviolet rays to photocuring the light.
  • the irradiation amount of ultraviolet light may be, for example, about 20 to about 600 mJ / cm 2 or about 50 to about 500 mJ / cm 2 .
  • the ultraviolet light source is not particularly limited as long as it can be used in the art to which the present technology belongs, and for example, a high pressure mercury lamp, a metal halide lamp, a black light fluorescent lamp, or the like can be used.
  • the irradiation may be performed for about 30 seconds to about 15 minutes, or about 1 minute to about 10 minutes for photocuring.
  • the thickness of the first hard coat layer may be about 50 to about 300 / ⁇ , or about 50 to about 200 / zm, or about 50 to about 150 /, or about 70 to about 150 after fully cured.
  • the first hard coat layer by including the first hard coat layer, it is possible to provide a hard coat film having a high hardness without deterioration of the curl characteristics.
  • a second hard coating composition comprising the above-mentioned components is applied to the other side of the support base, that is, the back side.
  • the applied agent
  • the irradiation amount of ultraviolet rays may be, for example, about 20 to about 600 mJ / cm 2 , or about 50 to about 500 mJ / cm 2 .
  • the light source for ultraviolet irradiation is not particularly limited as long as it can be used in the art to which the present technology belongs, and for example, a high pressure mercury lamp, a metal halide lamp, a black light fluorescent lamp, or the like can be used. Irradiation for about 30 seconds to about 15 minutes, or about 1 minute to about 10 minutes with the above irradiation amount may be carried out photocuring.
  • the second hardcoat layer may have a thickness of about 50 to about 300 ⁇ , or about 50 to about 200, or about 50 to about 150 3 ⁇ 4m, or about 70 to about 150 after fully cured.
  • the order of applying and photocuring the first and second hard coat compositions may be changed.
  • the hard coating layer according to the present invention is hard to generate curls or stacks even when formed in a high thickness on the substrate, it is possible to obtain a hard coating film having high transparency and layer resistance.
  • the hard coat film of the present invention may have excellent hardness and layer resistance enough to replace glass.
  • the hard coat film of the present invention may have excellent hardness and layer resistance enough to replace glass.
  • the hard coat film of the present invention may have excellent hardness and layer resistance enough to replace glass.
  • the second hard coat layer has a pencil hardness of at least 7H, or at least 8H, at a load of 1 kg, or
  • the second hard coating layer in the film containing the hard coating filling of the present invention the scratch after the reciprocating 400 times with a load of 500g after mounting the steel wool (0000) to the friction tester (steel wool) # 0000 It can occur up to two.
  • the hard coat film of the present invention the light transmittance is 91.0% or more, or
  • the haze may be 1.0% or less, or 0.5% or less, or 4% or less.
  • the initial color b value may be 1.0 or less.
  • the difference between the initial color b value and the color b value after 72 hours or more exposure to the UV lamp in the UVB wavelength region may be 0.5 or less, or 0.4 or less.
  • the hard coating film of the present invention when exposed to a temperature more than 70 hours at a temperature of 50 ° C or more and 80% or more and placed in a plane, the distance of each corner or one side of the hard coating film spaced apart from the plane
  • the maximum value may be about 1.0 mm or less, or about 0.6 mm or less, or about () .3 mm or less. see Specifically, the maximum value of the distance spaced from each corner or one side of the hard-coating film when placed in a plane after exposure to a temperature of 50 to 90 ° C and a humidity of 80 to 90% for 70 to 100 hours About 1.0 mm or less, or about 0.6 mm or less, or about 0.3 mm or less.
  • the hard coat film of the present invention exhibits high hardness, layer resistance, scratch resistance, high transparency, durability, light resistance, high transmittance, and the like, and thus may be usefully used in various fields.
  • the hard coat film of the present invention can be utilized in various fields.
  • the present invention can be used for a touch panel of a mobile communication terminal, a smartphone or a tablet PC, and a cover substrate or an element substrate of various displays.
  • the weight average molecular weight of the obtained polyrotasein was 600,000 g / mol, and elongation measured by ASTM D638 was 20%.
  • Example 1 The weight average molecular weight of the obtained polyrotasein was 600,000 g / mol, and elongation measured by ASTM D638 was 20%.
  • TMPTA trimethyl propane triacrylate
  • POPTA polyrotasein of Preparation Example 1
  • photoinitiator trade name: Darocur TPO
  • benzotriazole yellowing inhibitor trade name: Timivin 400
  • fluorine-based surfactant (Brand name: FC4430) 0.05 g
  • Methyl ethyl ketone lg was mixed to prepare a first hard coat composition.
  • HSA Hydroxyethyl acrylate 2g
  • the particle diameter is 20-30nm nano silica is 40 parts by weight 0/0 dispersed silica-dipentaerythritol hex the EPO Li acrylate (DPHA) complex 8g (silica 3.2g, DPHA 4.8g) 0.2 g of a photoinitiator (trade name: Darocur TPO), a yellow benzotriazole yellowing inhibitor (trade name: Tinuvin 400) O.lg, and 0.05 g of a fluorine-based surfactant (trade name: FC4430) were mixed to prepare a second hard coating composition.
  • DPHA dispersed silica-dipentaerythritol hex the EPO Li acrylate
  • DPHA dispersed silica-dipentaerythritol hex the EPO Li acrylate (DPHA) complex 8g (silica 3.2g, DPHA 4.8g) 0.2 g of
  • the second hard coating composition was applied onto a PET support substrate having a thickness of 15 cm X 20 cm, 188 mm 3.
  • the first photocuring was carried out by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • the first hard coating composition was applied to the back side of the supporting substrate.
  • a second photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp to prepare a hard coat film.
  • the thicknesses of the first and second hard coat layers formed on both sides of the resin were 100 m each.
  • Example 3 In the first hard coating composition, 4 g of a urethane acrylate polymer (trade name: UA200PA, Shinnakamura Chemical, weight average molecular weight 2,600 g / mol, elongation 170% according to ASTM D638) was used instead of 4 g of polyrotacein of Preparation Example 1. Except that a hard coat film was prepared in the same manner as in Example 1.
  • a urethane acrylate polymer trade name: UA200PA, Shinnakamura Chemical, weight average molecular weight 2,600 g / mol, elongation 170% according to ASTM D638
  • Example 4 In the first hard coating composition, 4 g of urethane acrylate-based polymer (trade name: UA340P, Shinnakamura Chemical, weight average molecular weight 13,000 g / mol, elongation according to ASTM D6 38 ) instead of 4 g of polyrotasein of Preparation Example 1 was added. A hard coat film was prepared in the same manner as in Example 1 except that it was used.
  • urethane acrylate-based polymer trade name: UA340P, Shinnakamura Chemical, weight average molecular weight 13,000 g / mol, elongation according to ASTM D6 38
  • DPHA dipentaerythritol EPO Li acrylate
  • TMPTA dispersed silica-trimethyl propane tri acrylate
  • Example 6 After the curing was completed in Example 1, except that the thickness of the first and second hard coat layer formed on both sides of the resin to 150, respectively, a hard coat film was prepared in the same manner as in Example 1.
  • Example 6 After the curing was completed in Example 1, except that the thickness of the first and second hard coat layer formed on both sides of the resin to 150, respectively, a hard coat film was prepared in the same manner as in Example 1.
  • TMPTA trimethylolpropane triacrylate
  • polyrotasein of Preparation Example 1 photoinitiator
  • benzotriazole-based yellowing inhibitor brand name: Tinuvin 400
  • FC4430 fluorine-based surfactant
  • hydroxyethyl acrylate HSA
  • silica silica dispersed in nano silica having a particle diameter of 20-30 nm 4 g of nucleoacrylate (DPHA) complex (3.2 g of silica, DPHA 4.8 g)
  • DPHA nucleoacrylate
  • a second hard coat composition was prepared by mixing 0.2 g of the initiator (trade name: Darocur TPO), O.lg, a benzotriazole-based yellowing inhibitor (trade name: Tinuvin 400), and 0.05 g of a fluorine-based surfactant (trade name: FC4430).
  • the second hardcoat composition was applied onto a PET support substrate of 15 cm ⁇ 20 cm, thickness 188 rni.
  • the first photocuring was carried out by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • the first hard coating composition was applied to the back side of the supporting substrate.
  • a second photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp to prepare a hard coat film.
  • the thickness of the first hard coat layer was 125 / mm and the thickness of the second hard coat layer was 100 / ⁇ . Comparative Example 1
  • the second hard coat composition of Example 1 was applied onto a PET support substrate having a thickness of 15 cm ⁇ 20 cm, 188 / t.
  • the first photocuring was carried out by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp.
  • Example 2 The second hard coating composition of Example 1 was applied to the back side of the supporting substrate. Next, a second photocuring was performed by irradiating ultraviolet rays of 280-350nm wavelength using a black light fluorescent lamp to prepare a hard coat film. After curing was completed, the thickness of the hard coat layers formed on both sides of the resin was 100 zm, respectively. Comparative Example 2
  • TMPTA Trimethyl to propane triacrylate
  • photoinitiator trade name: Darocur TPO
  • benzotriazole yellowing inhibitor trade name: Tinuvin 400
  • fluorine-based surfactant trade name: FC4430
  • Example 1 The second hard coat composition and the remaining process was the same as in Example 1 to prepare a hard coat film.
  • the main components in the hard coat films of Examples 1 to 6 and Comparative Examples 1 to 2 are shown in Table 1 below.
  • the number of grooves was evaluated after reciprocating 400 times with a load of 0.5 kg with respect to the second hard coating layer. It was evaluated as 0 when there are two or less home houses, ⁇ when two or more home houses and two or less than five home houses, and X when there are five or more home houses.
  • Each hard coating film was cut into 10 cm ⁇ 10 cm, stored in a chamber at a temperature of 85 ° C. and a humidity of 85% for 72 hours, and the maximum value of the distance at which one side of each corner was spaced apart from the plane was measured.
  • Each hard coating film was wound on a cylindrical lteltel having a diameter of lcm, with the first hard coating layer facing outward, and then cracks were determined to determine whether cracks were generated and X was evaluated as a case where cracks were not generated.
  • Comparative Examples 1 and 2 which do not include a second hard coating layer comprising a second crosslinked copolymer of 1 to 6 functional acrylate-based monomers and a photocurable elastomer have no impact resistance. .

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US20150299505A1 (en) 2015-10-22
WO2014030845A1 (ko) 2014-02-27
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